| Name | Relationship | Address | Signature | Signature date | CIK |
|---|---|---|---|---|---|
| Barnes Michael Gene | Executive Chairman, Director, 10%+ Owner | C/O TIPTREE INC., 660 STEAMBOAT ROAD, GREENWICH | /s/ Neil C. Rifkind, as Attorney-in-fact for Michael Barnes | 2025-09-12 | 0001498811 |
| Type | Sym | Class | Transaction | Value $ | Shares | Change % | * Price $ | Shares After | Date | Ownership | Footnotes |
|---|---|---|---|---|---|---|---|---|---|---|---|
| transaction | TIPT | Common Stock | Options Exercise | $264K | +46.5K | +0.47% | $5.67 | 10M | Sep 12, 2025 | Direct | F1 |
| transaction | TIPT | Common Stock | Tax liability | -$264K | -10.3K | -0.1% | $25.49 | 10M | Sep 12, 2025 | Direct | F2, F3 |
| transaction | TIPT | Common Stock | Options Exercise | $27.3K | +4.65K | +0.05% | $5.87 | 10M | Sep 12, 2025 | Direct | F1 |
| transaction | TIPT | Common Stock | Tax liability | -$27.3K | -1.07K | -0.01% | $25.49 | 10M | Sep 12, 2025 | Direct | F3, F4 |
| transaction | TIPT | Common Stock | Options Exercise | $745K | +112K | +1.12% | $6.65 | 10.1M | Sep 12, 2025 | Direct | F1 |
| transaction | TIPT | Common Stock | Tax liability | -$745K | -29.2K | -0.29% | $25.49 | 10.1M | Sep 12, 2025 | Direct | F3, F5 |
| Type | Sym | Class | Transaction | Value $ | Shares | Change % | * Price $ | Shares After | Date | Underlying Class | Amount | Exercise Price | Ownership | Footnotes |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| transaction | TIPT | January 2016 Stock Option | Options Exercise | -$264K | -46.5K | -100% | $5.67 | 0 | Sep 12, 2025 | Common Stock | 46.5K | $5.67 | Direct | F6, F7 |
| transaction | TIPT | March 2016 Stock Option | Options Exercise | -$27.3K | -4.65K | -100% | $5.87 | 0 | Sep 12, 2025 | Common Stock | 4.65K | $5.87 | Direct | F8, F9 |
| transaction | TIPT | February 2017 Stock Option | Options Exercise | -$745K | -112K | -100% | $6.65 | 0 | Sep 12, 2025 | Common Stock | 112K | $6.65 | Direct | F10, F11 |
| Id | Content |
|---|---|
| F1 | The transactions reported above in Table I reflect the cashless exercise of stock options. The cashless exercise for the options is reported in two lines. The lines coded M in column 3 of Table I report in column 4 the number of shares issuable upon exercise of the options had cash been paid to exercise the options, together with the exercise price with Code A for acquired. The lines coded F in column 3 of Table I relates to the same cashless exercise on the preceding line and reports in Column 4 the number of shares deducted from the total number of shares issuable to pay for the cashless exercise of such options with Code D for disposed. |
| F2 | Reflects 10,343 shares withheld by the Issuer at the market price of $25.49 per share less an exercise price of $5.67 per share to fund the cashless exercise of 46,494 options. |
| F3 | Represents the closing stock price as of the transaction date. |
| F4 | Reflects 1,071 shares withheld by the Issuer at the market price of $25.49 per share less an exercise price of $5.87 per share to fund the cashless exercise of 4,649 options. |
| F5 | Reflects 29,224 shares withheld by the Issuer at the market price of $25.49 per share less an exercise price of $6.65 per share to fund the cashless exercise of 112,015 options. |
| F6 | On January 4, 2016, the Reporting Person was granted non-qualified stock options to purchase 46,494 shares of common stock of the Registrant at $5.67 per share, subject to the terms of a Stock Option Agreement. |
| F7 | The option shares are fully vested and exercisable as of January 4, 2021. |
| F8 | On March 10, 2016, the Reporting Person was granted non-qualified stock options to purchase 4,649 shares of common stock of the Registrant at $5.87 per share, subject to the terms of a Stock Option Agreement. |
| F9 | The option shares are fully vested and exercisable as of March 10, 2021. |
| F10 | On February 22, 2017, the Reporting Person was granted non-qualified stock options to purchase 112,015 shares of common stock of the Registrant at $6.65 per share, subject to the terms of a Stock Option Agreement. |
| F11 | The option shares are fully vested and exercisable as of February 22, 2022. |